Are you implying that the more difficult path is always the higher, better, or "morally superior" one?

That is an obvious error. Suffering is not a good in itself. Otherwise:

I agree.  We follow our reason and not our emotions.  His decision was emotionally moving, and it took a great deal of virtue, subjectively speaking, to take that action (it speaks well to his heroic virtue), but when analyzed objectively, I don't see how that was the correct decision.  It would be one thing if he didn't have a family that he was bound to support in justice (along with the Communists' unjust possession and withholding of the money).  Commies were clearly not paying the laborer for his wages, a sin crying out to heaven for vengeance, and they were using their money to fund oppression of people.  In fact, to bring down a Commie government, it would not be immoral for a hacker to go into their bank accounts and drain them.  Now, the hacker would have no right to keep the money, but would be totally justified in draining the account.  In this case, the gentleman WOULD be entitled to the money, since he was being defrauded of being able to support his family.  I can see no way to slice this issue intellectually that would make what he did the objectively correct decision.

So you give the Commies their money back so they can, what?, use it to oppress even more people.  Hey, let me buy some extra torture equipment for the jail.

Here's another example.  I can barely support my family and from day to day they're at risk of going hungry.  I get some odd job and make a little money.  On my way home, I see a beggar and am moved with pity and give him some or all of the money.  While it was "generous" in one sense, he was actually defrauding his own family of what he owed them in justice.  That action was actually IMMORAL.  Sure, the guy was moved with generosity, etc.  If he just had to support himself, that would be great.  But since he owes that money in justice to his family, he's basically committing theft from his family to do this "noble deed".

One possibility that I would have to weigh if I were in Mr. Anastasius' position would be to question whether the over-payment was in fact an attempt at entrapment, an excuse to haul me back to prison.

That would be a prudential consideration.  It doesn't sound from the narrative as if that was his motivation, and whoever wrote the obit seemed to present it as an act of virtue (out of moral considerations) rather than motivated by what you say.  But that's a very good point.  It may have been unwise to keep the money for those reasons.

When your family is on the edge of starvation, yes, absolutely.  You have an obligation in justice to provide for your family, and no obligation in justice to return the money.  So the objectively "morally superior" option would have been to keep the money.

If your family was starving and some drug dealer dropped a sachel filled with cash, would you go, "Hey, Mr. Drug Dealer, you dropped your money."  That would actually to be an enabler of additional criminal operations.  He'd undoubtedly reinvest that money for more merchandise to sell.  That drug dealer was in unjust possession of the money in the first place, and there's no obligation in justice to give his money back.  Weighed against your obligation in justice to feed your family, it's a no brainer.  Those Communists were in unjust possession of the money and were unjustly withholding a reasonable living wage.  Not to mention that they were using the money to propagate their errors and oppress people.  They had zero right to that money and therefore there's zero obligation to return it.  In the meantime, your family is on the verge of starvation.

I can definitely understand the argument for him keeping the money, given that they had kept him in prison and all that for so long. There is definitely a case that he was "owed" the money, even if the communists wouldn't have agreed with that. It's obvious that their authority was not a lawful one. 

In the case of the drug dealer's money, wouldn't you be obligated to turn the money in to a source of lawful authority (assuming one was available to you)?

My understanding is that you wouldn't have a rightful claim to the money, even if you needed it in that case. Maybe I am incorrect here? 

I was just pointing out the danger of associating

More suffering = better, higher, morally superior

Because then those things I listed would all be saintly and virtuous, but they are not.

Suffering only has value for heaven because it causes us to increase our love of God, the virtue of charity (God-like love). But there are limits to what ways we can pursue more suffering -- that was my point.

If suffering were simpliciter good for its own sake, then any means of procuring more of it would be the higher path.

Agere contra (working against your natural inclinations) is only good sometimes. I am inclined to maintain familial and marital harmony. My lower nature indeed wants this, but -- believe it or not -- God wants this for me as well. Sometimes what I want, and what God wants for me (1st choice) are the same thing! Not always, but sometimes.

I suppose the dividing line here would be something like:

Suffering caused by your own sin is a temporal punishment that isn't gaining you any merit. It would be better if you had not committed the sin in the first place, because sin is bad, and that is why you must suffer. 

Suffering caused by standing up for a moral cause is not a punishment. It is pleasing to God and also meritorious. 

There is also suffering that just happens in the world as a result of sin, even to people who haven't "earned" it. This is not in its own right a good thing, but if you accept it with humility it can also be meritorious. God's permissive will allows for this. 

Being thrown in a camp by random chance would fall in the third category (random suffering as a result of sin). Being thrown in a camp because you refused to denounce God would be the second (suffering for a moral cause). Finally, being thrown in a camp because you kept money overpaid to you would likely be the first category (suffering caused by personal sin), unless maybe it instead counted as random suffering? 

This is actually a really interesting topic so it would be interesting to hear if you guys think this formulation is correct or not.